organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N′-[(E)-(4-Bromo-2-thien­yl)methyl­­idene]benzohydrazide 0.06-hydrate

aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and cDepartment of Chemistry, Government College University, Lahore, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 12 September 2009; accepted 15 September 2009; online 19 September 2009)

The title compound, C12H9BrN2OS·0.06H2O, is a hydrated Schiff base derived from benzoic hydrazide and 4-bromo­thio­phene-2-carboxaldehide. The two Schiff base mol­ecules in the asymmetric unit differ crystallographically: in one mol­ecule the dihedral angle between the benzene ring and thio­phene ring is 49.88 (11)°, whereas the other mol­ecule the rings are almost coplanar with an r.m.s. deviation for the non-H atoms of 0.025 Å. In the crystal, mol­ecules form polymeric sheets linked by N—H⋯O and C—H⋯O hydrogen bonds. The water mol­ecule of crystallization is partially occupied and its H atoms could not be located.

Related literature

For a related structure, see: Aldoshin et al. (1991[Aldoshin, S. M., Chuev, I. I., Atovmyan, L. O., Nedzvetskii, V. S. & Kulikov, A. S. (1991). Russ. Chem. Bull. 40, 87-90.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9BrN2OS·0.06H2O

  • Mr = 310.30

  • Monoclinic, P 21 /c

  • a = 8.8348 (4) Å

  • b = 18.3446 (10) Å

  • c = 15.6788 (6) Å

  • β = 90.274 (2)°

  • V = 2541.1 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 3.38 mm−1

  • T = 296 K

  • 0.28 × 0.14 × 0.12 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.573, Tmax = 0.664

  • 13354 measured reflections

  • 4719 independent reflections

  • 2848 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.077

  • S = 1.00

  • 4719 reflections

  • 316 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O2 0.86 2.06 2.878 (3) 160
N3—H3A⋯O1i 0.86 2.12 2.951 (3) 162
C6—H6⋯O2 0.93 2.50 3.231 (4) 136
C20—H20⋯O1i 0.93 2.49 3.282 (4) 143
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information


Comment top

The title compound (I, Fig. 1), has been prepared for complexation with various metals and with hope that it will be biologically active as well. The biological studies of (I) are under progress.

The crystal structure of (I) differs from (II) (N'-2-(thienylidene))benzhydrazide (Aldoshin et al., 1991) due to bromo substitution.

The title compound consist of two crystallographically different molecules and fractional part of O-atom which occupies the solvent accessible area. The fractional O-atom may be part of methanol, ethanol or water from air. The molecules are stabilized in the form of polymeric sheets due to H-bondings (Table 1, Fig. 2) which extend along the c axis. In one molecule the benzene ring A (C1—C6) and the thiophene ring B (C9—C10, S1) are oriented at a dihedral angle of 49.88 (11)° whereas in the other molecule both rings are nearly planar with an r.m.s. deviation of 0.025 Å.

Related literature top

For a related structure, see: Aldoshin et al. (1991).

Experimental top

To a hot stirred solution of benzoic hydrazide (1.36 g, 0.01 mol) in ethanol (15 ml) was added 4-bromo-2-thiophencarboxaldehide (1.91 g, 0.01 mol). The resultant mixture was then heated under reflux. After an hour precipitates were formed. The reaction mixture was further heated about 30 min for the completion of the reaction which was monitored through TLC. The reaction mixture was cooled to room temperature, filtered and washed with hot ethanol. The crude material was recrystallized in hot methanol to affoard colourless needles of (I).

Refinement top

There exist solvent accessible volume if only two Schiff base molecules are refined. Therefore, the largest difference peak was taken as a water O-atom and refined anisotropically with an occupancy factor of 0.125. Its presumed H atoms could not be located.

The other H-atoms were positioned geometrically with N—H = 0.86, C—H = 0.93 Å for aromatic H atoms and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C, N).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radius.
[Figure 2] Fig. 2. The partial packing of (I) which shows that molecules form polymeric chains which are extending along the crystallographic c axis.
N'-[(E)-(4-Bromo-2-thienyl)methylidene]benzohydrazide 0.06-hydrate top
Crystal data top
C12H9BrN2OS·0.06H2OF(000) = 1236
Mr = 310.30Dx = 1.622 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4719 reflections
a = 8.8348 (4) Åθ = 2.3–25.5°
b = 18.3446 (10) ŵ = 3.38 mm1
c = 15.6788 (6) ÅT = 296 K
β = 90.274 (2)°Cut needle, colourless
V = 2541.1 (2) Å30.28 × 0.14 × 0.12 mm
Z = 8
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4719 independent reflections
Radiation source: fine-focus sealed tube2848 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 7.80 pixels mm-1θmax = 25.5°, θmin = 2.3°
ω scansh = 109
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 2221
Tmin = 0.573, Tmax = 0.664l = 1818
13354 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0274P)2 + 0.0751P]
where P = (Fo2 + 2Fc2)/3
4719 reflections(Δ/σ)max = 0.001
316 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
C12H9BrN2OS·0.06H2OV = 2541.1 (2) Å3
Mr = 310.30Z = 8
Monoclinic, P21/cMo Kα radiation
a = 8.8348 (4) ŵ = 3.38 mm1
b = 18.3446 (10) ÅT = 296 K
c = 15.6788 (6) Å0.28 × 0.14 × 0.12 mm
β = 90.274 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4719 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2848 reflections with I > 2σ(I)
Tmin = 0.573, Tmax = 0.664Rint = 0.048
13354 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.077H-atom parameters constrained
S = 1.00Δρmax = 0.28 e Å3
4719 reflectionsΔρmin = 0.42 e Å3
316 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br10.14491 (5)0.59765 (2)0.12678 (2)0.0630 (2)
S10.17094 (11)0.36619 (5)0.06330 (5)0.0498 (3)
O10.1624 (3)0.11321 (12)0.15983 (13)0.0533 (9)
N10.2332 (3)0.19770 (14)0.25615 (14)0.0408 (10)
N20.2058 (3)0.25339 (15)0.19887 (15)0.0417 (10)
C10.2702 (3)0.07061 (17)0.28937 (17)0.0336 (11)
C20.1990 (4)0.00419 (18)0.28690 (18)0.0451 (14)
C30.2485 (4)0.05279 (19)0.3370 (2)0.0556 (14)
C40.3746 (5)0.0433 (2)0.3873 (2)0.0596 (14)
C50.4483 (4)0.0227 (2)0.39020 (19)0.0510 (16)
C60.3950 (4)0.08002 (18)0.34119 (18)0.0414 (11)
C70.2158 (3)0.12853 (18)0.22989 (19)0.0370 (12)
C80.2124 (3)0.31748 (18)0.22827 (19)0.0424 (11)
C90.1899 (3)0.37935 (18)0.17201 (18)0.0393 (11)
C100.1825 (3)0.45039 (18)0.1922 (2)0.0449 (11)
C110.1601 (3)0.49531 (17)0.1202 (2)0.0396 (11)
C120.1528 (4)0.45763 (18)0.0468 (2)0.0460 (12)
Br20.53100 (5)0.45182 (2)0.37441 (3)0.0758 (2)
S20.15815 (11)0.29933 (6)0.33933 (5)0.0559 (4)
O20.3874 (3)0.24667 (12)0.40780 (13)0.0479 (9)
N30.2504 (3)0.31281 (14)0.50045 (14)0.0415 (10)
N40.1274 (3)0.31373 (15)0.44655 (14)0.0434 (11)
C130.5098 (4)0.28364 (18)0.53558 (17)0.0366 (11)
C140.5227 (4)0.3363 (2)0.59883 (19)0.0513 (14)
C150.6512 (4)0.3403 (2)0.6488 (2)0.0640 (18)
C160.7682 (4)0.2919 (3)0.6359 (2)0.0684 (19)
C170.7573 (4)0.2400 (2)0.5739 (3)0.0623 (17)
C180.6284 (4)0.23582 (18)0.5242 (2)0.0497 (14)
C190.3774 (4)0.27852 (17)0.47561 (19)0.0360 (12)
C200.0191 (4)0.3547 (2)0.47003 (19)0.0494 (16)
C210.1191 (4)0.35979 (19)0.42087 (18)0.0451 (11)
C220.2347 (4)0.4067 (2)0.4320 (2)0.0497 (14)
C230.3549 (4)0.3943 (2)0.3754 (2)0.0490 (14)
C240.3311 (4)0.3383 (2)0.3225 (2)0.0564 (16)
O30.911 (2)0.0164 (9)0.1129 (9)0.048 (7)0.125
H1N0.260890.207130.307640.0489*
H20.116120.002460.250910.0537*
H30.197210.097070.336750.0669*
H40.410620.082020.419920.0714*
H50.533230.028780.424760.0612*
H60.443470.124980.343240.0496*
H80.231660.324970.285970.0509*
H100.191110.468070.247580.0536*
H120.139320.478870.006570.0548*
H3A0.246310.333860.549390.0496*
H140.444000.369130.607540.0619*
H150.659000.375640.691190.0765*
H160.854920.294670.669540.0818*
H170.836600.207590.565150.0746*
H180.621290.200090.482320.0594*
H200.029210.381940.519780.0592*
H220.234690.443310.472970.0597*
H240.400300.322540.281560.0676*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0723 (3)0.0383 (2)0.0784 (3)0.0020 (2)0.0096 (2)0.0086 (2)
S10.0682 (7)0.0444 (6)0.0368 (5)0.0061 (5)0.0025 (4)0.0047 (4)
O10.0733 (18)0.0508 (16)0.0357 (13)0.0143 (13)0.0168 (12)0.0050 (11)
N10.0569 (19)0.0380 (18)0.0274 (14)0.0006 (14)0.0068 (12)0.0069 (13)
N20.0497 (19)0.0413 (18)0.0340 (15)0.0028 (14)0.0042 (12)0.0099 (14)
C10.037 (2)0.038 (2)0.0259 (17)0.0035 (16)0.0034 (14)0.0021 (14)
C20.055 (3)0.042 (2)0.0382 (19)0.0052 (18)0.0015 (16)0.0039 (17)
C30.085 (3)0.031 (2)0.051 (2)0.007 (2)0.013 (2)0.0002 (18)
C40.087 (3)0.040 (2)0.052 (2)0.021 (2)0.010 (2)0.0125 (18)
C50.052 (3)0.056 (3)0.045 (2)0.013 (2)0.0027 (17)0.0107 (18)
C60.042 (2)0.042 (2)0.0403 (19)0.0007 (16)0.0022 (16)0.0043 (16)
C70.040 (2)0.038 (2)0.033 (2)0.0064 (16)0.0003 (16)0.0030 (16)
C80.050 (2)0.042 (2)0.0351 (19)0.0037 (17)0.0027 (15)0.0030 (17)
C90.043 (2)0.040 (2)0.0349 (19)0.0040 (16)0.0029 (15)0.0067 (15)
C100.048 (2)0.044 (2)0.0427 (19)0.0001 (18)0.0074 (16)0.0004 (18)
C110.038 (2)0.0307 (19)0.050 (2)0.0035 (15)0.0044 (16)0.0094 (17)
C120.048 (2)0.045 (2)0.045 (2)0.0010 (18)0.0016 (16)0.0156 (17)
Br20.0563 (3)0.0776 (3)0.0934 (3)0.0089 (2)0.0164 (2)0.0157 (2)
S20.0563 (7)0.0660 (7)0.0454 (5)0.0039 (5)0.0074 (4)0.0029 (5)
O20.0560 (16)0.0536 (16)0.0340 (12)0.0029 (12)0.0005 (11)0.0139 (12)
N30.0431 (19)0.054 (2)0.0273 (15)0.0011 (14)0.0061 (13)0.0039 (12)
N40.0431 (19)0.057 (2)0.0301 (16)0.0010 (15)0.0055 (14)0.0019 (13)
C130.041 (2)0.041 (2)0.0277 (18)0.0029 (16)0.0016 (15)0.0054 (15)
C140.046 (2)0.066 (3)0.042 (2)0.0023 (19)0.0008 (17)0.0057 (18)
C150.055 (3)0.097 (4)0.040 (2)0.010 (2)0.0129 (19)0.006 (2)
C160.051 (3)0.100 (4)0.054 (3)0.010 (3)0.017 (2)0.027 (2)
C170.053 (3)0.063 (3)0.071 (3)0.007 (2)0.002 (2)0.026 (2)
C180.056 (3)0.042 (2)0.051 (2)0.0013 (19)0.0012 (19)0.0075 (17)
C190.042 (2)0.034 (2)0.032 (2)0.0060 (16)0.0004 (16)0.0047 (15)
C200.053 (3)0.061 (3)0.034 (2)0.005 (2)0.0064 (18)0.0022 (17)
C210.050 (2)0.054 (2)0.0313 (19)0.0032 (19)0.0050 (17)0.0022 (16)
C220.051 (3)0.056 (2)0.042 (2)0.002 (2)0.0031 (18)0.0011 (18)
C230.048 (2)0.056 (3)0.043 (2)0.0053 (19)0.0058 (17)0.0147 (19)
C240.050 (3)0.070 (3)0.049 (2)0.016 (2)0.0162 (17)0.011 (2)
O30.058 (13)0.047 (12)0.039 (10)0.005 (9)0.010 (8)0.021 (8)
Geometric parameters (Å, º) top
Br1—C111.885 (3)C2—H20.9300
Br2—C231.880 (4)C3—H30.9300
S1—C91.729 (3)C4—H40.9300
S1—C121.705 (3)C5—H50.9300
S2—C211.726 (3)C6—H60.9300
S2—C241.706 (4)C8—H80.9300
O1—C71.226 (4)C10—H100.9300
O2—C191.217 (4)C12—H120.9300
N1—N21.381 (4)C13—C141.389 (4)
N1—C71.343 (4)C13—C191.500 (5)
N2—C81.264 (4)C13—C181.379 (5)
N1—H1N0.8600C14—C151.378 (5)
N3—N41.374 (4)C15—C161.378 (6)
N3—C191.346 (4)C16—C171.364 (6)
N4—C201.273 (4)C17—C181.379 (5)
N3—H3A0.8600C20—C211.444 (5)
C1—C21.372 (5)C21—C221.348 (5)
C1—C71.492 (4)C22—C231.399 (5)
C1—C61.377 (4)C23—C241.338 (5)
C2—C31.378 (5)C14—H140.9300
C3—C41.373 (5)C15—H150.9300
C4—C51.375 (5)C16—H160.9300
C5—C61.384 (5)C17—H170.9300
C8—C91.451 (4)C18—H180.9300
C9—C101.343 (5)C20—H200.9300
C10—C111.411 (4)C22—H220.9300
C11—C121.344 (4)C24—H240.9300
C9—S1—C1291.19 (16)N2—C8—H8120.00
C21—S2—C2491.20 (17)C9—C10—H10124.00
N2—N1—C7118.7 (2)C11—C10—H10124.00
N1—N2—C8116.3 (2)S1—C12—H12124.00
N2—N1—H1N121.00C11—C12—H12124.00
C7—N1—H1N121.00C14—C13—C19123.5 (3)
N4—N3—C19119.1 (2)C14—C13—C18118.4 (3)
N3—N4—C20115.0 (2)C18—C13—C19118.0 (3)
C19—N3—H3A120.00C13—C14—C15120.5 (3)
N4—N3—H3A120.00C14—C15—C16119.9 (3)
C6—C1—C7122.3 (3)C15—C16—C17120.3 (3)
C2—C1—C6119.6 (3)C16—C17—C18119.8 (3)
C2—C1—C7118.0 (3)C13—C18—C17121.2 (3)
C1—C2—C3120.9 (3)O2—C19—C13121.2 (3)
C2—C3—C4119.1 (3)O2—C19—N3122.8 (3)
C3—C4—C5120.9 (3)N3—C19—C13116.0 (3)
C4—C5—C6119.4 (3)N4—C20—C21121.3 (3)
C1—C6—C5120.1 (3)S2—C21—C20121.3 (3)
N1—C7—C1116.5 (3)C20—C21—C22127.7 (3)
O1—C7—C1121.2 (3)S2—C21—C22110.9 (3)
O1—C7—N1122.3 (3)C21—C22—C23112.8 (3)
N2—C8—C9120.0 (3)Br2—C23—C22122.7 (3)
S1—C9—C8120.2 (2)Br2—C23—C24124.0 (3)
C8—C9—C10128.5 (3)C22—C23—C24113.4 (3)
S1—C9—C10111.3 (2)S2—C24—C23111.7 (3)
C9—C10—C11112.7 (3)C13—C14—H14120.00
C10—C11—C12113.0 (3)C15—C14—H14120.00
Br1—C11—C10123.2 (2)C14—C15—H15120.00
Br1—C11—C12123.8 (2)C16—C15—H15120.00
S1—C12—C11111.9 (2)C15—C16—H16120.00
C3—C2—H2120.00C17—C16—H16120.00
C1—C2—H2120.00C16—C17—H17120.00
C4—C3—H3120.00C18—C17—H17120.00
C2—C3—H3120.00C13—C18—H18119.00
C5—C4—H4120.00C17—C18—H18119.00
C3—C4—H4120.00N4—C20—H20119.00
C4—C5—H5120.00C21—C20—H20119.00
C6—C5—H5120.00C21—C22—H22124.00
C1—C6—H6120.00C23—C22—H22124.00
C5—C6—H6120.00S2—C24—H24124.00
C9—C8—H8120.00C23—C24—H24124.00
C12—S1—C9—C8179.4 (2)N2—C8—C9—C10175.0 (3)
C12—S1—C9—C100.1 (2)S1—C9—C10—C110.5 (3)
C9—S1—C12—C110.3 (3)C8—C9—C10—C11179.7 (3)
C24—S2—C21—C220.5 (3)C9—C10—C11—Br1179.94 (19)
C21—S2—C24—C230.8 (3)C9—C10—C11—C120.8 (4)
C24—S2—C21—C20176.9 (3)Br1—C11—C12—S1179.84 (17)
C7—N1—N2—C8174.8 (3)C10—C11—C12—S10.7 (4)
N2—N1—C7—O17.3 (4)C18—C13—C14—C150.1 (5)
N2—N1—C7—C1170.5 (2)C19—C13—C14—C15176.5 (3)
N1—N2—C8—C9178.0 (2)C14—C13—C18—C170.3 (5)
C19—N3—N4—C20171.6 (3)C19—C13—C18—C17176.4 (3)
N4—N3—C19—O21.6 (5)C14—C13—C19—O2159.0 (3)
N4—N3—C19—C13176.5 (3)C14—C13—C19—N319.1 (5)
N3—N4—C20—C21178.4 (3)C18—C13—C19—O217.4 (5)
C6—C1—C2—C31.5 (5)C18—C13—C19—N3164.4 (3)
C7—C1—C2—C3176.7 (3)C13—C14—C15—C160.2 (5)
C2—C1—C6—C50.2 (5)C14—C15—C16—C170.1 (6)
C7—C1—C6—C5174.8 (3)C15—C16—C17—C180.3 (6)
C2—C1—C7—O131.2 (4)C16—C17—C18—C130.4 (6)
C6—C1—C7—N134.0 (4)N4—C20—C21—S211.7 (5)
C2—C1—C7—N1150.9 (3)N4—C20—C21—C22171.4 (3)
C6—C1—C7—O1143.9 (3)S2—C21—C22—C230.1 (4)
C1—C2—C3—C42.6 (5)C20—C21—C22—C23177.1 (3)
C2—C3—C4—C52.1 (5)C21—C22—C23—Br2179.1 (3)
C3—C4—C5—C60.5 (5)C21—C22—C23—C240.5 (4)
C4—C5—C6—C10.7 (5)Br2—C23—C24—S2178.73 (19)
N2—C8—C9—S15.8 (4)C22—C23—C24—S20.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.862.062.878 (3)160
N3—H3A···O1i0.862.122.951 (3)162
C6—H6···O20.932.503.231 (4)136
C20—H20···O1i0.932.493.282 (4)143
Symmetry code: (i) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC12H9BrN2OS·0.06H2O
Mr310.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)8.8348 (4), 18.3446 (10), 15.6788 (6)
β (°) 90.274 (2)
V3)2541.1 (2)
Z8
Radiation typeMo Kα
µ (mm1)3.38
Crystal size (mm)0.28 × 0.14 × 0.12
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.573, 0.664
No. of measured, independent and
observed [I > 2σ(I)] reflections
13354, 4719, 2848
Rint0.048
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.077, 1.00
No. of reflections4719
No. of parameters316
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.42

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.862.062.878 (3)160
N3—H3A···O1i0.862.122.951 (3)162
C6—H6···O20.932.503.231 (4)136
C20—H20···O1i0.932.493.282 (4)143
Symmetry code: (i) x, y+1/2, z+1/2.
 

Acknowledgements

AH greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a scholarship under the Indigenous PhD Program (PIN 063–121531-PS3–127).

References

First citationAldoshin, S. M., Chuev, I. I., Atovmyan, L. O., Nedzvetskii, V. S. & Kulikov, A. S. (1991). Russ. Chem. Bull. 40, 87–90.  Google Scholar
First citationBruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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